In 2000, Luckovich started his comic-strip "SuperZeros", about a pair of dim-witted superheroes. It was distributed by Tribune Media Service and lasted a year.

In a September 2001 interview, Luckovich commented on his style of cartooning and how it changed after the 9/11 terrorist attacks:

Normally with my cartoons I try to use humor to get across my point. After Sept. 11th, you just couldn't use humor. The tragedy was so enormous, you couldn't be funny. It's almost like you have to come up with cartoons using a different part of your brain. I was just trying to come up with images that expressed the emotions that I was feeling and tried to focus in on different aspects of the tragedy that I thought were important.

In that same interview Luckovich cited Jeff MacNelly as his "biggest editorial cartoonist role model" and Mort Drucker as his "first hero."

Luckovich attracted a great deal of backlash when the newspaper cartoonist drew a cartoon depicting Michael Jackson's death one day after his death. The comic strip illustrated the leaders Heaven and Hell flipping a coin to see where the late King of Pop would be after his demise. Many people, including Jackson's family, friends, and fans deemed the cartoon offensive.[1]

Luckovich also recently generated controversy when depicting an image of two police officers, one holding a sign reading "Miranda Rights" intended for "white people", the other holding a sign reading "Last Rites" intended for "black people". The image was hosted in an August 2016 issue of the Boston Globe.